8,628

Summerland Key, FL Homes

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  • /14

    $258,000

    • Land

    701 Spanish Main Dr Unit LOT 317, Cudjoe Key, FL 33042

    Venture Out RV Lot - Prime Location Near the StoreOpportunity to own a spacious RV lot in the highly desirable Venture Out community in Cudjoe Key. This pie-shaped lot measures approximately 65' x 67' x 63', offering generous space for your RV, outdoor living area, and parking.Conveniently located just a short distance from the community store and amenities, this lot provides easy access to

    Lisa Carter Florida Keys Realty, Inc.

    701 Spanish Main Dr Unit LOT 317, Cudjoe Key, FL 33042
  • /38

    $700,000 Sold Jan 29, 2026

    24830 Park Dr, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,188 Sq Ft
    • Built 2015

    Last Sold Summary

    • 3% Below List Price
    • $589/SF
    • 7 Days On Market

    Current Estimated Value $706,712

    Last Listing Agent Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)

    24830 Park Dr, Summerland Key, FL 33042
    • /81

      Est $1,309,362 Not Listed For Sale

      23041 Snapper Ln, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,664 Sq Ft
      • Built 1992
      23041 Snapper Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 19% Below List Price
      • $977/SF
      • 11 Days On Market

      Last Sold Price $1,625,000

      Last Listing Agent Tommy Mack Coastal Collection Real Estate Inc.

  • /110

    $2,800,000 New Construction

    • 3 Beds
    • 3 Baths
    • 2,100 Sq Ft

    1553 Sunrise Dr, Big Pine Key, FL 33043

    Walk into this luxurious palace with captivating open water views. Light colors accenting the beautiful interior with matching large porcelain floors enhancing the large windows bringing the natural light inside. Gourmet kitchen for any chef to create great memories viewing the sunsets. Open patio with a great view of the pool and the outdoor entertaining areas. Three roomy suites for your family

    Barbara Eads Barbara Eads Realty

    1553 Sunrise Dr, Big Pine Key, FL 33043
  • /35

    $902,500 Sold Apr 11, 2025

    346 Blackbeard Rd, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,188 Sq Ft
    • Built 1996

    Last Sold Summary

    • 8% Below List Price
    • $760/SF
    • 62 Days On Market

    Current Estimated Value $919,038

    Last Listing Agent Sandra Tuttle Island Welcome Real Estate

    346 Blackbeard Rd, Summerland Key, FL 33042
    • /19

      Est $818,477 Not Listed For Sale

      22910 Privateer Dr, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 960 Sq Ft
      • Built 1988
      22910 Privateer Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 3% Below List Price
      • $881/SF
      • 58 Days On Market

      Last Sold Price $846,000

      Last Listing Agent Robin Nilsson Keller Williams Key West Compass Realty

  • /51

    $837,500 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,250 Sq Ft

    29115 Rose Dr, Big Pine Key, FL 33043

    Welcome to this meticulously maintained and updated move-in ready canal-front home that offers the perfect blend of comfort, style, and durability. Featuring an inviting open-concept floor plan, this home boasts three spacious bedrooms and two modern bathrooms, all enhanced by LVP flooring throughout. Built above flood level with just the right number of steps to climb, this home ensures both

    Dave Wiley Coldwell Banker Schmitt Real Estate Co. (KW)

    29115 Rose Dr, Big Pine Key, FL 33043
  • /72

    $3,436,000 Sold May 16, 2025

    5460 Dorn Rd, Summerland Key, FL 33042

    • 3 Beds
    • 3 Baths
    • 2,134 Sq Ft
    • Built 1996

    Last Sold Summary

    • 7% Below List Price
    • $1,610/SF
    • 30 Days On Market

    Current Estimated Value $3,497,907

    Last Listing Agent Sandra Tuttle Island Welcome Real Estate

    5460 Dorn Rd, Summerland Key, FL 33042
    • /2

      Est $1,533,495 Not Listed For Sale

      27362 Anguila Ln, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,842 Sq Ft
      • Built 1975
      27362 Anguila Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 14% Below List Price
      • $964/SF

      Last Sold Price $1,775,000

      Last Listing Agent Carolyn Quelly Coastal Collection Real Estate Inc.

  • /57

    $1,495,000

    • 2 Beds
    • 2 Baths
    • 1,392 Sq Ft

    25368 2nd St, Summerland Key, FL 33042

    Experience the perfect blend of character, durability, and Keys style at this quintessential cottage on the oceanside of Summerland Key. This thoughtfully crafted home welcomes you with the warmth of original Miami-Dade cypress floors and soaring ceilings that fill the interior with a sense of openness and timeless charm. Designed for peace of mind, the property boasts a metal roof, Hardie board

    Ally Kelley Ocean Sotheby's International Realty

    25368 2nd St, Summerland Key, FL 33042
  • /32

    $1,282,100 Sold Nov 04, 2025

    32857 Tortuga Ln, Big Pine Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 1994

    Last Sold Summary

    • 8% Below List Price
    • $916/SF
    • 23 Days On Market

    Current Estimated Value $1,301,439

    Last Listing Agent Madeleine Lowe Expert Realty LLC (HQ)

    32857 Tortuga Ln, Big Pine Key, FL 33043
    • /12

      Est $623,691 Not Listed For Sale

      27007 Angelfish Rd, Summerland Key, FL 33042

      • 2 Beds
      • 1,201 Sq Ft
      • Built 1967
      27007 Angelfish Rd, Summerland Key, FL 33042

      Last Sold Summary

      • 108% Above List Price
      • $250/SF
      • 281 Days On Market

      Last Sold Price $300,000

      Last Listing Agent Sabrina Liguori Key West Vacation Properties & Realty, LLC (KW)

  • /27

    $350,000

    • 2 Beds
    • 1 Bath
    • 672 Sq Ft

    701 Spanish Main Dr Unit 566, Cudjoe Key, FL 33042

    Canal-front opportunity in Venture Out! This 1 bedroom / 1 bath property offers a 17' seawall and endless potential for future use. Whether you're envisioning a personal Keys retreat or re-imagining the space as an RV lot, this property provides flexibility in a highly desirable, gated waterfront community. Enjoy all Venture Out amenities including marina access, boat ramp, pools, recreational

    Bea Evelyn Citron Compass Florida, LLC

    701 Spanish Main Dr Unit 566, Cudjoe Key, FL 33042
  • /35

    $560,000 Sold Aug 29, 2025

    19616 Aztec St, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,129 Sq Ft
    • Built 1953

    Last Sold Summary

    • 20% Below List Price
    • $496/SF
    • 196 Days On Market

    Current Estimated Value $575,808

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    19616 Aztec St, Summerland Key, FL 33042
    • /34

      Est $879,566 Not Listed For Sale

      320 Spanish Main Dr, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,056 Sq Ft
      • Built 1989
      320 Spanish Main Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 3% Below List Price
      • $862/SF
      • 18 Days On Market

      Last Sold Price $910,000

      Last Listing Agent Sean Farrer Coldwell Banker Schmitt Real Estate Co. (KW)

  • /7

    $799,990

    • Land
    • 0.18 Acre
    • $4,444,389 per Acre

    28525 Jolly Roger Dr, Little Torch Key, FL 33042

    RARE opportunity to own a build ready canal front lot in the heart of Little Torch Key. Tucked away on a quiet dead end road near the end of the island, this prime waterfront parcel offers the best of both worlds! Open water views from the front and a deep canal with seawall along the back. Enjoy unobstructed ocean and sky views from your front porch with no homes across the street ever, creating

    Fazana Haniff FHG Realty, LLC.

    28525 Jolly Roger Dr, Little Torch Key, FL 33042
  • /2

    $357,000 Sold Nov 07, 2025

    31145 Hibiscus Dr, Big Pine Key, FL 33043

    • Land

    Last Sold Summary

    • 11% Below List Price
    • 222 Days On Market

    Current Estimated Value $355,556

    Last Listing Agent Cheryl Moses Action Keys Realty of the Lower FL Keys LLC

    31145 Hibiscus Dr, Big Pine Key, FL 33043
    • /41

      Est $391,406 Not Listed For Sale

      701 Spanish Main Dr Unit 416, Cudjoe Key, FL 33042

      701 Spanish Main Dr Unit 416, Cudjoe Key, FL 33042

      Last Sold Summary

      • 4% Below List Price
      • 95 Days On Market

      Last Sold Price $408,000

      Last Listing Agent Lisa Carter Florida Keys Realty, Inc.

  • /84

    $1,599,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,648 Sq Ft

    17125 Wahoo Ln, Summerland Key, FL 33042

    Canal-front living with 100 feet of waterfront, gorgeous kitchen, and your own private pool in the heart of Sugarloaf Key. This updated 3 bedroom, 2 bath plus office or 4th bedroom, canal-front pool home on prestigious Sugarloaf Key offers 100 feet of waterfrontage and excellent boating access. This beautiful residence features a new concrete pool with sunshelf, new tiki hut, new metal roof, and

    Lisa Swanson The Agency Florida Keys

    17125 Wahoo Ln, Summerland Key, FL 33042
  • /10

    $2,000,000 Sold Jul 14, 2025

    441 Airport Dr N, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 2,256 Sq Ft
    • Built 2001

    Last Sold Summary

    • 13% Below List Price
    • $887/SF
    • 166 Days On Market

    Current Estimated Value $2,036,812

    Last Listing Agent Jonathan Minerick Homecoin.com

    441 Airport Dr N, Summerland Key, FL 33042
    • /37

      Est $885,501 Not Listed For Sale

      139 Le Grand Ln, Summerland Key, FL 33042

      • 3 Beds
      • 1 Bath
      • 1,300 Sq Ft
      • Built 1994
      139 Le Grand Ln, Summerland Key, FL 33042

      Last Sold Summary

      • $684/SF
      • 48 Days On Market

      Last Sold Price $889,000

      Last Listing Agent Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  • /47

    $445,000

    • Land

    701 Spanish Main Dr Unit LOT 496, Cudjoe Key, FL 33042

    ROGO exempt RV Lot 496 - Waterfront Lot in Venture Out, Cudjoe Key, Mile Marker 23Bring your RV or build your Florida Keys dream home without the hassle of going through the ROGO process.Waterfront RV lot located in the gated community of Venture Out on Cudjoe Key. Lot 496 has a concrete pad, offering a durable, low-maintenance surface ideal for RV parking and outdoor living.The property features

    Lanny Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit LOT 496, Cudjoe Key, FL 33042
  • /50

    $1,599,000 Sold Jun 10, 2025

    29655 Forrestal Ave, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 1,932 Sq Ft
    • Built 1990

    Last Sold Summary

    • 6% Below List Price
    • $828/SF
    • 42 Days On Market

    Current Estimated Value $1,621,142

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    29655 Forrestal Ave, Big Pine Key, FL 33043
    • /27

      Est $1,664,887 Not Listed For Sale

      22836 Port Royal Ln, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,406 Sq Ft
      • Built 1987
      22836 Port Royal Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 17% Above List Price
      • $1,422/SF
      • 6 Days On Market

      Last Sold Price $2,000,000

      Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  • /29

    $639,900

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft

    31124 Avenue C, Big Pine Key, FL 33043

    Welcome to an inviting, well-priced island home in Big Pine Key, perfectly suited for families, military buyers, or anyone seeking relaxed Florida Keys living with modern upgrades already done. This beautifully renovated 2-bedroom, 2-bath home was thoughtfully updated in 2024 and blends comfort, privacy, and tropical charm.Inside, you'll find new luxury vinyl flooring throughout, a refreshed

    Dawn McComish Lokation Real Estate

    31124 Avenue C, Big Pine Key, FL 33043
  • /54

    $615,000 Sold Jul 11, 2025

    701 Spanish Main Dr Unit 131, Cudjoe Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft
    • Built 1999

    Last Sold Summary

    • 14% Below List Price
    • $712/SF
    • 194 Days On Market

    Last Listing Agent Jan Fritz Coldwell Banker Schmitt RE Co.

    701 Spanish Main Dr Unit 131, Cudjoe Key, FL 33042
    • /37

      Est $902,377 Not Listed For Sale

      81 Coral Ave, Summerland Key, FL 33042

      • 2 Beds
      • 3 Baths
      • 1,535 Sq Ft
      • Built 1988
      81 Coral Ave, Summerland Key, FL 33042

      Last Sold Summary

      • 16% Above List Price
      • $505/SF
      • 13 Days On Market

      Last Sold Price $775,000

      Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  • /9

    $3,500,000

    • Land

    19657 Seminole St, Sugarloaf Key, FL 33042

    Unique Waterfront Property with Opportunity to Build Your Dream MansionWelcome to your once-in-a-lifetime opportunity to own a truly exceptional waterfront property in the Florida Keys. This expansive property boasts a total of 3 lots ensuring unparalleled potential for building your waterfront mansion.Property comes with build back letter. There's not another property like this south of

    Derek Epperly Engel & Volkers Key West

    19657 Seminole St, Sugarloaf Key, FL 33042
  • /40

    $635,000 Sold Aug 29, 2025

    31148 Avenue C, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 1,272 Sq Ft
    • Built 2003

    Last Sold Summary

    • 9% Below List Price
    • $499/SF
    • 212 Days On Market

    Current Estimated Value $648,051

    Last Listing Agent Sandra Rodriguez Lokation Real Estate

    31148 Avenue C, Big Pine Key, FL 33043
    • /34

      Est $755,735 Not Listed For Sale

      28551 Buccaneer Rd, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 841 Sq Ft
      • Built 1976
      28551 Buccaneer Rd, Summerland Key, FL 33042

      Last Sold Summary

      • 1% Above List Price
      • $892/SF
      • 48 Days On Market

      Last Sold Price $750,000

      Last Listing Agent Monika Rydzak eXp Realty LLC KW Branch

  • /61

    $2,299,000 Open Sat 10AM - 1PM

    • 3 Beds
    • 3 Baths
    • 2,167 Sq Ft

    556 Caribbean Dr E, Summerland Key, FL 33042

    MOTIVATED SELLERS! The sea writes the script at this 3 bed, 3 bath oceanfront retreat on the most highly sought after neighborhoods on Summerland Key, and it stands in a class of its own. Western exposure delivers nightly golden-hour performances over the Atlantic, while deep-draft boating--among the best this side of the 7-Mile Bridge--begins right from your backyard. You'll love deep channel

    Angelina Will Berkshire Hathaway HomeServices Knight & Gardner Realty

    556 Caribbean Dr E, Summerland Key, FL 33042
  • /58

    $1,164,000 Sold Dec 12, 2025

    164 Tortuga Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 1990

    Last Sold Summary

    • 3% Below List Price
    • $831/SF
    • 27 Days On Market

    Current Estimated Value $1,158,151

    Last Listing Agent Michele Adams Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

    164 Tortuga Ln, Summerland Key, FL 33042
    • /45

      Est $1,975,971 Not Listed For Sale

      20942 6th Ave W, Summerland Key, FL 33042

      • 3 Beds
      • 3 Baths
      • 2,772 Sq Ft
      • Built 1994
      20942 6th Ave W, Summerland Key, FL 33042

      Last Sold Summary

      • 16% Above List Price
      • $613/SF
      • 42 Days On Market

      Last Sold Price $1,700,000

      Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  • /35

    $799,000

    • 3 Beds
    • 3 Baths
    • 1,224 Sq Ft

    3672 Fox St, Big Pine Key, FL 33043

    Discover a peaceful Keys escape on a quiet canal in Big Pine Key. This attractive 3-bedroom, 3-bath home blends relaxed, nature-forward living with modern comforts.Bright, open living area with high ceilingsUpdated kitchen with stainless steel appliances, granite counters, and ample cabinetry. Private master suite with en-suite bath and direct balcony access.Two additional bedrooms ideal for

    Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

    3672 Fox St, Big Pine Key, FL 33043
  • /2

    $570,000 Sold Jul 17, 2025

    3767 Hibiscus St, Big Pine Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft
    • Built 1986

    Last Sold Summary

    • 4% Below List Price
    • $594/SF
    • 6 Days On Market

    Current Estimated Value $622,245

    Last Listing Agent Ryan Call REALTY ZOOM

    3767 Hibiscus St, Big Pine Key, FL 33043
    • /43

      Est $1,072,609 Not Listed For Sale

      17055 Kingfish Ln W, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,184 Sq Ft
      • Built 1988
      17055 Kingfish Ln W, Summerland Key, FL 33042

      Last Sold Summary

      • 2% Above List Price
      • $921/SF
      • 38 Days On Market

      Last Sold Price $1,090,000

      Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  • /53

    $1,710,000

    • 4 Beds
    • 2 Baths
    • 2,605 Sq Ft

    1481 Sugarloaf Blvd, Summerland Key, FL 33042

    Welcome to this spacious canal-front retreat set on an oversized half-acre lot with endless potential. This four-bedroom, 2,605 sq ft home offers a rare combination of water access, outdoor living, and privacy.Enjoy true Florida Keys living with a private concrete boat ramp, a dock, and direct canal access leading to mangrove-lined creeks and open water just minutes away. Whether you're exploring

    Jenna Stauffer Ocean Sotheby's International Realty

    1481 Sugarloaf Blvd, Summerland Key, FL 33042
  • /44

    $876,000 Sold Apr 29, 2025

    30751 Palm Dr, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 1,724 Sq Ft
    • Built 1990

    Last Sold Summary

    • 6% Below List Price
    • $508/SF
    • 156 Days On Market

    Current Estimated Value $923,434

    Last Listing Agent Melissa Graham Bluescape Real Estate

    30751 Palm Dr, Big Pine Key, FL 33043
    • /50

      Est $916,957 Not Listed For Sale

      17396 Jamaica Ln, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,224 Sq Ft
      • Built 1992
      17396 Jamaica Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 14% Above List Price
      • $660/SF
      • 1 Day On Market

      Last Sold Price $807,500

      Last Listing Agent Sarah Eckert Coldwell Banker Schmitt Real Estate Co. (KW)

  • /25

    $695,000

    • Land

    28587 Peg Leg Rd Little Torch Aly, Little Torch Key, FL 33042

    Vacant Land on Canal waiting on permit 41.5 points today for a 3497 sq.foot house with a roof top area. Permit number# SFDUP -2025-0096 Four-bedroom three-bathroom house. Builder will build for the buyer price and terms to be negotiated Dock and plans are included. Ranked for next quarter to be delivered a permit. Pictures shown as built house.

    Barbara Eads Barbara Eads Realty

    28587 Peg Leg Rd Little Torch Aly, Little Torch Key, FL 33042

Showing Results 521 - 560, Page 14 of 18

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